scholarly journals Structure Elucidation and Cholinesterase Inhibition Activity of Two New Minor Amaryllidaceae Alkaloids

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1279
Author(s):  
Jana Maříková ◽  
Abdullah Al Mamun ◽  
Latifah Al Shammari ◽  
Jan Korábečný ◽  
Tomáš Kučera ◽  
...  
Keyword(s):  
Active Sites ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Cholinesterase Inhibition ◽  
Inhibition Activity ◽  
Amaryllidaceae Alkaloids ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Narcissus Pseudonarcissus ◽  
Inhibition Potency

Two new minor Amaryllidaceae alkaloids were isolated from Hippeastrum × hybridum cv. Ferrari and Narcissus pseudonarcissus cv. Carlton. The chemical structures were identified by various spectroscopic (one- and two-dimensional (1D and 2D) NMR, circular dichroism (CD), high-resolution mass spectrometry (HRMS) and by comparison with literature data of similar compounds. Both isolated alkaloids were screened for their human acetylcholinesterase (hAChE) and butyrylcholinesterase (hBuChE) inhibition activity. One of the new compounds, a heterodimer alkaloid of narcikachnine-type, named narciabduliine (2), showed balanced inhibition potency for both studied enzymes, with IC50 values of 3.29 ± 0.73 µM for hAChE and 3.44 ± 0.02 µM for hBuChE. The accommodation of 2 into the active sites of respective enzymes was predicted using molecular modeling simulation.

scholarly journals Alkaloids from Chlidanthus fragrans and their Acetylcholinesterase, Butyrylcholinesterase and Prolyl Oligopeptidase Activities

2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Lucie Cahlíková ◽  
Martina Hrabinová ◽  
Andrea Kulhánková ◽  
Nina Benešová ◽  
Jakub Chlebek ◽  
...  
Keyword(s):  
Nmr Assignments ◽  
2D Nmr ◽  
Inhibition Activity ◽  
Prolyl Oligopeptidase ◽  
Biological Assays ◽  
Amaryllidaceae Alkaloids ◽  
Chemical Structures ◽  
Ellman’S Method ◽  
Butyrylcholinesterase Inhibition

Eleven Amaryllidaceae alkaloids (1–11) were isolated from fresh bulbs of Chlidanthus fragrans Herb. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic experiments. Complete NMR assignments were achieved for deoxypretazzetine (1). All compounds were evaluated for their erythrocytic acetylcholinesterase and serum butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro- p-nitroanilide was used as substrate. In biological assays, only the crinine type Amaryllidaceae alkaloid undulatine showed promising acetylcholinesterase and prolyl oligopeptidase inhibition activity with IC50 values of 23.0 ± 1.0 μM and 1.96 ± 0.12 mM, respectively. Other isolated compounds were considered inactive.

scholarly journals Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽  
2022 ◽  
Vol 20 (1) ◽  
pp. 51
Author(s):  
Senhua Chen ◽  
Heng Guo ◽  
Minghua Jiang ◽  
Qilin Wu ◽  
Jing Li ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Selective Cytotoxicity ◽  
X Ray ◽  
Planar Structures ◽  
Spectroscopic Analyses ◽  
Ic50 Values ◽  
Anti Inflammatory ◽  
Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

scholarly journals Mono-/Bis-Alkenoic Acid Derivatives From an Endophytic Fungus Scopulariopsis candelabrum and Their Antifungal Activity

2022 ◽  
Vol 9 ◽  
Author(s):  
Jun Tang ◽  
Xueshuang Huang ◽  
Ming-Hang Cao ◽  
Zhiyan Wang ◽  
Zhiyin Yu ◽  
...  
Keyword(s):  
Candida Albicans ◽  
Minimum Inhibitory Concentration ◽  
Inhibitory Concentration ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Positive Control ◽  
Diffusion Method ◽  
Exserohilum Turcicum ◽  
Chemical Structures ◽  
Alkenoic Acid

During a screening for antifungal secondary metabolites, six new mono-/bis-alkenoic acid derivatives (2–7) and one known alkenoic acid derivative (1) were isolated from an endophytic fungi Scopulariopsis candelabrum. Their chemical structures were identified by 1H-NMR, 13C-NMR, 2D NMR, and high-resolution mass spectrometry, as well as comparisons with previously reported literatures. Among them, fusariumesters C‒F (2–5) are bis-alkenoic acid derivatives dimerized by an ester bond, while acetylfusaridioic acid A (6) and fusaridioic acid D (7) are alkenoic acid monomers. All the isolates were submitted to an antifungal assay against Candida albicans and the corn pathogen Exserohilum turcicum using the filter paper agar diffusion method. As a result, only compound 1 decorating with β-lactone ring turned out to be active against these two tested fungi. The broth microdilution assay against Candida albicans showed the minimum inhibitory concentration (MIC) value of 1 to be 20 μg/ml, while the minimum inhibitory concentration value of the positive control (naystatin) was 10 μg/ml. And the half maximal inhibitory concentration (IC50) value (21.23 μg/ml) of 1 against Exserohilum turcicum was determined by analyzing its inhibition effect on the mycelial growth, using cycloheximide (IC50 = 46.70 μg/ml) as the positive control.

scholarly journals New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 439 ◽  
Author(s):  
Li ◽  
Peifer ◽  
Janussen ◽  
Tasdemir
Keyword(s):  
Anticancer Activity ◽  
Deep Sea ◽  
Topoisomerase I ◽  
Active Sites ◽  
Binding Potential ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Ft Ir ◽  
The Antarctic

The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation process guided by bioactivity and molecular networking-based metabolomics yielded three known discorhabdins, (−)-discorhabdin L (1), (+)-discorhabdin A (2), (+)-discorhabdin Q (3), and three new discorhabdin analogs (−)-2-bromo-discorhabdin D (4), (−)-1-acetyl-discorhabdin L (5), and (+)-1-octacosatrienoyl-discorhabdin L (6) from the MeOH-soluble portion of the organic extract. The chemical structures of 1–6 were elucidated by extensive NMR, HR-ESIMS, FT-IR, [α]D, and ECD (Electronic Circular Dichroism) spectroscopy analyses. Compounds 1, 5, and 6 showed promising anticancer activity with IC50 values of 0.94, 2.71, and 34.0 µM, respectively. Compounds 1–6 and the enantiomer of 1 ((+)-discorhabdin L, 1e) were docked to the active sites of two anticancer targets, topoisomerase I-II and indoleamine 2,3-dioxygenase (IDO1), to reveal, for the first time, the binding potential of discorhabdins to these proteins. Compounds 5 and 6 are the first discorhabdin analogs with an ester function at C-1 and 6 is the first discorhabdin bearing a long-chain fatty acid at this position. This study confirms Latrunculia sponges to be excellent sources of chemically diverse discorhabdin alkaloids.

scholarly journals Chemical Constituents of Stems and Leaves of Tagetespatula L. and Its Fingerprint

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3911 ◽  
Author(s):  
Yu-Meng Wang ◽  
Xiao-Ku Ran ◽  
Muhammad Riaz ◽  
Miao Yu ◽  
Qian Cai ◽  
...  
Keyword(s):  
High Performance ◽  
High Resolution Mass Spectrometry ◽  
Chemical Constituents ◽  
Human Gastric Cancer ◽  
Chemical Structures ◽  
Yellow Color ◽  
Ic50 Values ◽  
Gastric Cancer Cell Lines ◽  
Stems And Leaves

Tagetespatula L. is a widely cultivated herbal medicinal plant in China and other countries. In this study, two new 2, 3-dihydrobenzofuran glucosides (1, 2) and fourteen known metabolites (3–16) were isolated from the stems and leaves of T. patula (SLT). The chemical structures of the isolated compounds were characterized comprehensively based on one- and two-dimensional NMR spectroscopy and high resolution mass spectrometry. Absolute configurations of compounds 1 and 2 were determined by ECD calculations. Compounds 1 and 2 exhibited moderate in vitro inhibitory activities against human gastric cancer cell lines (AGS) with IC50 values of 41.20 μmol/L and 30.43 μmol/L, respectively. The fingerprint profiles of stems and leaves of T. patula with three color types of flowers (Janie Yellow Bright, Jinmen Orange, Shouyao Red and Yellow color) were established by high-performance liquid chromatography (HPLC). Ten different batches of stems and leaves were examined as follow: Shouyao Red and Yellow color (1, 2, 3), Janie Yellow Bright (4, 5, 6, 7) and Jinmen Orange (8, 9, 10). Twenty-two common peaks were identified with similarity values ranging from 0.910 to 0.977. Meanwhile, the average peak area of SLT in the three types of flowers was different and it was the highest in Janie Yellow Bright.

scholarly journals Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 581
Author(s):  
Vangelis Smyrniotopoulos ◽  
Christian Merten ◽  
Daria Firsova ◽  
Howard Fearnhead ◽  
Deniz Tasdemir
Keyword(s):  
Cell Line ◽  
Brown Seaweed ◽  
Cancer Cell Line ◽  
Structural Diversity ◽  
Chemical Study ◽  
2D Nmr ◽  
Chemical Structures ◽  
Bifurcaria Bifurcata ◽  
Ic50 Values ◽  
Ft Ir

Brown alga Bifurcaria bifurcata is a prolific source of bioactive acyclic (linear) diterpenes with high structural diversity. In the continuation of our investigations on Irish brown algae, we undertook an in-depth chemical study on the n-hexanes and chloroform subextracts of B. bifurcata that led to isolation of six new (1–6) and two known (7–8) acyclic diterpenes. Chemical structures of the compounds were elucidated by a combination of 1D and 2D NMR, HRMS, FT-IR, [α]D and vibrational circular dichroism (VCD) spectroscopy. Compounds 1–8, as well as three additional linear diterpenes (9–11), which we isolated from the same seaweed before, were tested against the human breast cancer cell line (MDA-MB-231). Several compounds moderately inhibited the growth of the MDA-MB-231 cell line with IC50 values ranging from 11.6 to 32.0 μg/mL. The present study carried out on the lipophilic extracts of the Irish B. bifurcata shows the enormous capacity of this seaweed to produce a large palette of acyclic diterpenes with diverse oxygenation and substitution patterns and promising bioactivities.

scholarly journals Amaryllidaceae Alkaloids of Belladine-Type from Narcissus pseudonarcissus cv. Carlton as New Selective Inhibitors of Butyrylcholinesterase

Biomolecules ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 800 ◽  
Author(s):  
Abdullah Al Mamun ◽  
Jana Maříková ◽  
Daniela Hulcová ◽  
Jiří Janoušek ◽  
Marcela Šafratová ◽  
...  
Keyword(s):  
Selective Inhibition ◽  
Structural Type ◽  
Amaryllidaceae Alkaloids ◽  
In Silico Studies ◽  
Ic50 Values ◽  
Narcissus Pseudonarcissus ◽  
20 Nm ◽  
Inhibition Pattern ◽  
In Vitro Data

Thirteen known (1–12 and 16) and three previously undescribed Amaryllidaceae alkaloids of belladine structural type, named carltonine A-C (13–15), were isolated from bulbs of Narcissus pseudonarcissus cv. Carlton (Amaryllidaceae) by standard chromatographic methods. Compounds isolated in sufficient amounts, and not tested previously, were evaluated for their in vitro acetylcholinesterase (AChE; E.C. 3.1.1.7), butyrylcholinesterase (BuChE; E.C. 3.1.1.8) and prolyl oligopeptidase (POP; E.C. 3.4.21.26) inhibition activities. Significant human BuChE (hBUChE) inhibitory activity was demonstrated by newly described alkaloids carltonine A (13) and carltonine B (14) with IC50 values of 913 ± 20 nM and 31 ± 1 nM, respectively. Both compounds displayed a selective inhibition pattern for hBuChE with an outstanding selectivity profile over AChE inhibition, higher than 100. The in vitro data were further supported by in silico studies of the active alkaloids 13 and 14 in the active site of hBuChE.

scholarly journals Saccharobisindole, Neoasterric Methyl Ester, and 7-Chloro-4(1H)-quinolone: Three New Compounds Isolated from the Marine Bacterium Saccharomonospora sp.

Marine Drugs ◽  
2021 ◽  
Vol 20 (1) ◽  
pp. 35
Author(s):  
Sohee Kim ◽  
Tu Cam Le ◽  
Sang-Ah Han ◽  
Prima F. Hillman ◽  
Ahreum Hong ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Marine Bacterium ◽  
High Resolution Mass Spectrometry ◽  
Micrococcus Luteus ◽  
Culture Broth ◽  
Chemical Components ◽  
Inhibition Activity ◽  
Chemical Structures ◽  
New Compounds ◽  
And Staphylococcus Aureus

Analysis of the chemical components from the culture broth of the marine bacterium Saccharomonospora sp. CNQ-490 has yielded three novel compounds: saccharobisindole (1), neoasterric methyl ester (2), and 7-chloro-4(1H)-quinolone (3), in addition to acremonidine E (4), pinselin (5), penicitrinon A (6), and penicitrinon E (7). The chemical structures of the three novel compounds were elucidated by the interpretation of 1D, 2D nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS) data. Compound 2 generated weak inhibition activity against Bacillus subtilis KCTC2441 and Staphylococcus aureus KCTC1927 at concentrations of 32 μg/mL and 64 μg/mL, respectively, whereas compounds 1 and 3 did not have any observable effects. In addition, compound 2 displayed weak anti-quorum sensing (QS) effects against S. aureus KCTC1927 and Micrococcus luteus SCO560.

scholarly journals New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 100
Author(s):  
Sherif Ebada ◽  
Werner Müller ◽  
Wenhan Lin ◽  
Peter Proksch
Keyword(s):  
Spectral Analysis ◽  
Marine Sponge ◽  
Parent Compound ◽  
2D Nmr ◽  
Chemical Structures ◽  
Nmr Data ◽  
Ic50 Values ◽  
Nanomolar Range ◽  
Mouse Lymphoma

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

scholarly journals Alkaloids from Peumus boldus and their Acetylcholinesterase, Butyrylcholinesterase and Prolyl Oligopeptidase Inhibition Activity

2015 ◽  
Vol 10 (4) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Anna Hošt'álková ◽  
Lubomír Opletal ◽  
Jiří Kuneš ◽  
Zdeněk Novák ◽  
Martina Hrabinová ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Inhibition Activity ◽  
Isoquinoline Alkaloids ◽  
Prolyl Oligopeptidase ◽  
Benzylisoquinoline Alkaloids ◽  
Chemical Structures ◽  
Chromatographic Methods ◽  
Ellman’S Method ◽  
Butyrylcholinesterase Inhibition

Eleven isoquinoline alkaloids (1–11) were isolated from dried leaves of Peumus boldus Mol. by standard chromatographic methods. The chemical structures were elucidated by MS, and 1D and 2D NMR spectroscopic analysis, and by comparison with literature data. Compounds isolated in sufficient amount were evaluated for their acetylcholinesterase, and butyrylcholinesterase inhibition activity using Ellman's method. In the prolyl oligopeptidase assay, Z-Gly-Pro- p-nitroanilide was used as substrate. Promising butyrylcholinesterase inhibition activities were demonstrated by two benzylisoquinoline alkaloids, reticuline (8) and N-methylcoclaurine (9), with IC50 values of 33.6 ± 3.0 μM and 15.0 ± 1.4 μM, respectively. Important prolyl oligopeptidase inhibition activities were shown by N-methyllaurotetanine (6) and sinoacutine (4) with IC50 values of 135.4 ± 23.2 μM and 143.1 ± 25.4 μM, respectively. Other tested compounds were considered inactive.

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